(2R,3R,4S,5R,6R)-4-(benzyloxy)-6-((benzyloxy)methyl)-2-((bis(dimethylamino)phosphoryl)oxy)-5-(2-chloroacetoxy)tetrahydro-2H-pyran-3-yl benzoate | 201139-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4S,5R,6R)-4-(benzyloxy)-6-((benzyloxy)methyl)-2-((bis(dimethylamino)phosphoryl)oxy)-5-(2-chloroacetoxy)tetrahydro-2H-pyran-3-yl benzoate
• CAS: 201139-12-0
• 化学式: C₃₃H₄₀ClN₂O₉P
• 分子量: 675.115
• InChiKey: HYIKWVJZRREVLY-FLIKSIBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  46.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  113.07
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-[(E,2S,3R)-1-hydroxy-3-phenylmethoxyoctadec-4-en-2-yl]octadecanamide 、 (2R,3R,4S,5R,6R)-4-(benzyloxy)-6-((benzyloxy)methyl)-2-((bis(dimethylamino)phosphoryl)oxy)-5-(2-chloroacetoxy)tetrahydro-2H-pyran-3-yl benzoate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到[(2R,3R,4S,5R,6R)-5-(2-chloroacetyl)oxy-2-[(E,2S,3R)-2-(octadecanoylamino)-3-phenylmethoxyoctadec-4-enoxy]-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
  参考文献：
  名称：

  “Armed-disarmed” glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide

  摘要：

  A stereocontrolled synthesis of globotriaosylcernmide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting "armed-disarmed" glycosidation methodology bared on glycosyl donors and accepters carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl-(1-->4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10365-3
• 作为产物：
  描述：

  Benzoic acid (4aR,7R,8S,8aR)-6-allyloxy-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 在 吡啶 、 盐酸 、 正丁基锂 、 3 A molecular sieve 、 sodium acetate 、 sodium cyanoborohydride 、 palladium dichloride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 5.75h， 生成 (2R,3R,4S,5R,6R)-4-(benzyloxy)-6-((benzyloxy)methyl)-2-((bis(dimethylamino)phosphoryl)oxy)-5-(2-chloroacetoxy)tetrahydro-2H-pyran-3-yl benzoate
  参考文献：
  名称：

  “Armed-disarmed” glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide

  摘要：

  A stereocontrolled synthesis of globotriaosylcernmide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting "armed-disarmed" glycosidation methodology bared on glycosyl donors and accepters carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl-(1-->4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10365-3